Triethylamine → HCID 20800915, compound

HRID 1071391Notes

Reaction equation

HRID 1071391 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([O-:3])=[O:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:20]Br.C(N(CC)CC)C>ClCCl>[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:20][N:13]1[CH2:12][CH2:11][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1009491-(2-Nitrophenyl)piperazineHCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Product 1

HCID 20800915HCID 20800915, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-nitro-phenyl)-piperazine (4.53 g) (commercially from Emkachem) and 3,4-dichlorobenzyl bromide (4.6 g) in 100 mL of dichloromethane was treated with triethylamine (3.4 mL). The reaction was stirred at ambient temperature under inert atmosphere overnight. After solvent removal, the crude reaction mixture was subjected directly to flash chromatography using silica. Elution with hexanes, then 20% ethyl acetate in hexanes, and finally 33% ethyl acetate in hexanes furnished the product as an oil (6.4 g), which was carried on as is.

Workup

  1. customAfter solvent removal
  2. customthe crude reaction mixture
  3. washElution with hexanes

Sources & evidence

ORD record
ord-9a05cb04db0344d3bb6282f80cee75eb
Source dataset
uspto-grants-2005_06
Patent number
US06906073B2

Reaction notes

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